What happens when an ethnographic, cultural relativistic approach to arts funding runs head-on into a “fine arts” approach governed by assumptions of excellence, appropriate targets of funding, and methods of distributing funds? This chapter, based on twenty-three years (1978–2000) working at the National Endowment for the Arts, will respond to this question through my personal conceptual and methodological challenges and experiences. When the National Endowment for the Arts and National Endowment for the Humanities were created in 1965, there was talk of creating a third endowment for folklore. This effort was unsuccessful, but it points to the belief at the time that American folk art traditions would not be well served by the federal endowments. There was much truth to this, as I and my colleagues regularly bumped into “glass ceilings and walls” that silently worked against us in supporting our field of hundreds of cultural traditions and thousands of art forms. My ethnomusicological training and experience were invaluable, not only in understanding the art forms and responding to their needs, but also understanding the biases of the institutional culture in which we were housed. At the same time, while certain aspects of my training at UCLA helped in navigating the waters of arts funding, much of the knowledge I applied to my work was learned “on the job” in extra-academic activities and mentorships rather than in university courses and seminars. This line of reflection will yield observations and recommendations to improve training and to increase ethnomusicology’s applicability and social and cultural relevance.